Hydroxylamine → HCID 22625132, compound

Participants

Reaction Steps

To a vial containing aminoalcohol A (0.05 g, 0.21 mmol) prepared as in Example 13 was added a solution containing cyclopropanecarboxaldehyde (0.21 g, 3.0 mmol), toluene (3.0 mL), and 1 M diethylzinc in hexane (6.0 mL). After 3 days at room temperature, acetic anhydride (1.2 mL, 13 mmol) was added. After 2 additional days the mixture was diluted in ether (50 mL) and the reaction was quenched by dropwise addition of half-saturated aqueous ammonium chloride (50 mL). The ether layer was separated and the aqueous layer was further extracted with ether (2×50 mL). The combined ether layers were dried over magnesium sulfate whereupon the solvent was removed at reduced pressure. The residue was purified by flash chromatography on 220-400 mesh silica with 90% hexane and 10% ether as eluant. The product (+)-1-(cyclopropyl)propyl acetate (0.23 g, 54%) was isolated as a colorless liquid by distillation at reduced pressure. Anal. for C11H20O2. Calcd: C, 71.70; H, 10.94; found: C, 71.41; H, 10.69. 1H NMR (CDCl3/TMS): δ0.23 (m, 1 H), 0.36 (m, 1 H), 0.43 (m, 1 H), 0.52 (m, 1 H), 1.00-1.09 (m+t, 4 H total), 1.69 (m, 2 H), 2.05 (s, 3 H), 4.20 (m, 1 H); 13C NMR (CDCl3/TMS): δ2.66, 2.82, 9.57, 14.57, 21.03, 27.45, 79.62, 170.66. [α]D25=+26.2, c=1.04 g/100 mL chloroform. Chiral capillary gas chromatographic analysis at 55° C. on Cyclodex B stationary phase (J & W Scientific) indicated that the enantiomeric excess of the product was 96%.

Provenance & Evidence